EP3377588B1 - Strukturklebstoff mit verbessertem fehlermodus - Google Patents

Strukturklebstoff mit verbessertem fehlermodus Download PDF

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Publication number
EP3377588B1
EP3377588B1 EP16806385.7A EP16806385A EP3377588B1 EP 3377588 B1 EP3377588 B1 EP 3377588B1 EP 16806385 A EP16806385 A EP 16806385A EP 3377588 B1 EP3377588 B1 EP 3377588B1
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EP
European Patent Office
Prior art keywords
structural adhesive
adhesive film
composition
epoxy
thermosettable
Prior art date
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Active
Application number
EP16806385.7A
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English (en)
French (fr)
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EP3377588A1 (de
Inventor
Elisabeth Cura
Sohaib Elgimiabi
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3M Innovative Properties Co
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3M Innovative Properties Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/35—Heat-activated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/56—Polyhydroxyethers, e.g. phenoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2463/00—Presence of epoxy resin

Definitions

  • the structural adhesive film according to the present disclosure comprises a thermosettable composition that comprises an epoxy compound preferably having an average epoxy equivalent weight of less than 250 g/equivalent.
  • an epoxy compound preferably having an average epoxy equivalent weight of less than 250 g/equivalent.
  • Suitable epoxy compounds for use herein will be easily identified by those skilled in the art, in the light of the present description.
  • thermosettable composition of the structural adhesive film may further comprise one or more toughening agents.
  • Any toughening agent commonly known in the art, may be used in the thermosettable composition of the structural adhesive film of the disclosure.
  • the toughening agents are preferably selected from a group comprising core-shell toughening agents, CTBNs (carboxyl and/or nitrile terminated butadiene/nitrile rubbers) and high molecular weight amine terminated polytetramethylene oxide.
  • thermosettable composition A high molecular weight amine terminated polytetramethylene oxide useful in the thermosettable composition is commercially available, for example, from 3M Company, St. Paul/MN, USA, under the trade designation "3M EPX TM Rubber".
  • Another aspect of the present disclosure is a corrosion resistant structural adhesive film, comprising the structural adhesive composition as described herein.
  • the present disclosure relates to a method of making a metal part assembly, the method comprising:
  • the epoxy resin, the thermoplastic phenoxy resin and the core shell toughening agent are mixed together for 2 min, thereby yielding a masterbatch formulation with ratios as set forth in table 2.
  • This masterbatch is then placed into an air-driven oven at temperature of 95 °C for about 1 h.
  • the hot mixture is again stirred for 2 min at 3000 rpm in the speed mixer to ensure complete dispersion of the three ingredients.
  • the mixer temperature is reduced to 60°C and the two curatives together with the further ingredients as set forth in table 3 are added to the mixture, followed by mixing for an additional 2 minutes under vacuum.
  • the resulted mixture is a paste having a uniform consistency.
  • the mixer is hot coated to a film having thickness of 0.4 mm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Epoxy Resins (AREA)

Claims (11)

  1. Eine wärmehärtbare Strukturklebstoffzusammensetzung, umfassend
    (a) eine Epoxidverbindung;
    (b) eine thermoplastische Verbindung;
    (c) ein Epoxidhärtungsmittel;
    (d) nicht kugelförmige Teilchen,
    wobei die wärmehärtbare Strukturklebstoffzusammensetzung einen kohäsiven Fehlermodus in einem T-Schältest gemäß ASTM D1876 bereitstellt; und
    wobei die nicht kugelförmigen Teilchen eine Korngröße gemäß EN ISO 8130- 13:2010 im Bereich von 30 µm bis 200 µm aufweisen.
  2. Die Strukturklebstoffzusammensetzung nach Anspruch 1, wobei die nicht kugelförmigen Teilchen anorganische Teilchen sind, vorzugsweise aus Material bestehen, das aus Metall, Kohlenstoff und Glas ausgewählt ist.
  3. Die Strukturklebstoffzusammensetzung nach Anspruch 2, wobei der Kohlenstoff aus Graphit und Ruß, ausgewählt ist, vorzugsweise Graphit, stärker bevorzugt thermisch expandierbaren Graphit.
  4. Die Strukturklebstoffzusammensetzung nach einem der vorstehenden Ansprüche, wobei die nicht kugelförmigen Teilchen eine unregelmäßige Form oder Flockenform aufweisen.
  5. Die Strukturklebstoffzusammensetzung nach einem der vorstehenden Ansprüche, wobei die Zusammensetzung die nicht kugelförmigen Teilchen (d) in einer Menge von 0,1 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorzugsweise in einer Menge von 0,5 bis 7 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung, mehr bevorzugt in einer Menge von 1,0 bis 5 Gew.-%, bezogen auf das Gesamtgewicht der Zusammensetzung, umfasst.
  6. Die Strukturklebstoffzusammensetzung nach einem der Ansprüche 1 bis 5, die eine Überlappungsscherfestigkeit gemäß DIN EN 1465 von mindestens 21 MPa bei -40 °C und/oder von mindestens 17 MPa bei 23 °C und/oder mindestens 11 bei 80 °C und/oder einer T-Schälfestigkeit gemäß ASTM D1876 von mindestens 165 N, vorzugsweise mindestens 170 N, stärker bevorzugt mindestens 175 N, und/oder einen Tropfen der Überlappungsscherfestigkeit gemäß DIN EN 1465 nach Kataplasmabedingungen von 30 % oder weniger, vorzugsweise von 25 % oder weniger, stärker bevorzugt von 20 % oder weniger, noch stärker bevorzugt von 15 % oder weniger, bereitstellt.
  7. Eine Strukturklebstofffolie, umfassend die Strukturklebstoffzusammensetzung nach einem der Ansprüche 1 bis 6.
  8. Ein Verfahren zum Binden von Teilen, wobei das Verfahren die folgenden Schritte umfasst:
    i. Bereitstellen eines ersten Teils und eines zweiten Teils;
    ii. Bereitstellen einer Strukturklebstoffzusammensetzung nach einem der Ansprüche 1 bis 6 oder einer Strukturklebstofffolie nach Anspruch 7 an mindestens einer Oberfläche des ersten Teils und/oder des zweiten Teils,
    iii. Verkleben des ersten Teils und der zweiten Teile bei einer Temperatur unterhalb der Aktivierungstemperatur, die geringer als die Aktivierungstemperatur des Epoxidhärtungsmittels ist, wodurch eine Verbindung zwischen dem ersten und dem zweiten Teil gebildet wird, wobei vorzugsweise eine Metallverbindung zwischen dem ersten und dem zweiten Teil gebildet wird,
    iv. Erhitzen der Verbindung bei einer Temperatur, die höher als die Aktivierungstemperatur des Epoxidhärtungsmittels ist, um ein Wärmehärten der wärmehärtbaren Zusammensetzung zu bewirken.
  9. Eine Teileanordnung, umfassend
    (I) Ein erstes Teil und ein zweites Teil und
    (II) Eine wärmegehärtete Strukturklebstofffolie mit einem ersten Abschnitt nahe einem ersten Ende der Strukturklebstofffolie und einem zweiten Abschnitt nahe dem zweiten Ende gegenüber dem ersten Ende der Strukturklebstofffolie;
    wobei die wärmegehärtete Strukturklebstofffolie zwischen dem ersten Teil und dem zweiten Teil bereitgestellt ist und das erste Teil und das zweite Teil miteinander verklebt, und wobei die wärmegehärtete Strukturklebstofffolie durch Wärmehärten der wärmehärtbaren Zusammensetzung nach einem der Ansprüche 1 bis 6 oder der Strukturklebstofffolie nach Anspruch 7 erhalten wird.
  10. Das Verfahren nach Anspruch 8 oder Teileanordnung nach Anspruch 9, wobei das Material des ersten und/oder zweiten Teils ausgewählt ist aus Metall, Kohlenstoff, Polymermaterial, Verbundmaterialien, Holz und Glas, wobei vorzugsweise das Metall ausgewählt ist aus Stahl, Edelstahl, verzinktem Stahl, vernickeltem Stahl, Titan, Aluminium, Zink, Magnesium und deren Legierungen und Kombinationen davon.
  11. Verwendung einer wärmehärtbaren Strukturklebstoffzusammensetzung nach einem der Ansprüche 1 bis 6 oder einer wärmehärtbaren Strukturklebstofffolie nach Anspruch 7 zum Verkleben von Teilen bei Industrieanwendungen, vorzugsweise bei Rohbauverfahren.
EP16806385.7A 2015-11-19 2016-11-17 Strukturklebstoff mit verbessertem fehlermodus Active EP3377588B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP15195469.0A EP3170877B1 (de) 2015-11-19 2015-11-19 Strukturklebstoff mit verbessertem fehlermodus
PCT/US2016/062498 WO2017087651A1 (en) 2015-11-19 2016-11-17 Structural adhesive with improved failure mode

Publications (2)

Publication Number Publication Date
EP3377588A1 EP3377588A1 (de) 2018-09-26
EP3377588B1 true EP3377588B1 (de) 2023-05-03

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EP15195469.0A Active EP3170877B1 (de) 2015-11-19 2015-11-19 Strukturklebstoff mit verbessertem fehlermodus
EP16806385.7A Active EP3377588B1 (de) 2015-11-19 2016-11-17 Strukturklebstoff mit verbessertem fehlermodus

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US (1) US20180273811A1 (de)
EP (2) EP3170877B1 (de)
JP (3) JP2019503406A (de)
KR (1) KR20180083413A (de)
CN (1) CN108291130B (de)
BR (1) BR112018010315A2 (de)
CA (1) CA3005870A1 (de)
MX (1) MX2018006138A (de)
WO (1) WO2017087651A1 (de)

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WO2019005800A1 (en) * 2017-06-29 2019-01-03 3M Innovative Properties Company CURABLE COMPOSITION
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EP3587527A1 (de) 2018-06-30 2020-01-01 3M Innovative Properties Company Voll(per)fluorpolymere auskleidung für klebebänder
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JP7045768B2 (ja) 2019-04-03 2022-04-01 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
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JP2022084534A (ja) 2020-11-26 2022-06-07 信越化学工業株式会社 生体電極組成物、生体電極、生体電極の製造方法、及び反応複合体
JP2022106281A (ja) 2021-01-06 2022-07-19 信越化学工業株式会社 生体電極組成物、生体電極、及び生体電極の製造方法
EP4306558A1 (de) 2021-03-12 2024-01-17 Shin-Etsu Chemical Co., Ltd. Bioelektrode, herstellungsverfahren für bioelektrode und messverfahren für biosignale
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CN115678475A (zh) * 2022-11-17 2023-02-03 上海希奈新材料科技有限公司 一种阻燃耐水煮耐高低温冲击的双组份环氧灌封胶及制备方法和应用

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